Oakland Vacations from $307
Book a Hotel + Flight or Car together to unlock savings
Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Uniontown
Price was $385, price is now $307 per person
$307
per person
May 4 - May 7
found 16 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9/10 Wonderful! (603 reviews)
Room was clean, front desk was helpful with everything we needed and went beyond.
Reviewed on Jan 29, 2026
Etage Executive Living
Downtown Pittsburgh
Price was $1,258, price is now $423 per person
$423
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,483 reviews)
The staff was really nice. I love the room we were given especially since we got upgraded. But there were some minor things that were not up to my cleanliness standards. I found hair in my bed sheets.
Reviewed on Feb 21, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Feb 25 to Feb 26
$148 total
Feb 25 - Feb 26
Total with taxes and fees
9/10 Wonderful! (617 reviews)
Clean room and amazing reception
Reviewed on Feb 22, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$111 nightly
The price is $127 total per night from Feb 25 to Feb 26
$127 total
Feb 25 - Feb 26
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
The front desk staff were very nice, the room was clean, and check out was super easy.
Reviewed on Feb 18, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $222 total per night from Mar 22 to Mar 23
$222 total
Mar 22 - Mar 23
Total with taxes and fees
9.2/10 Wonderful! (743 reviews)
Autograph hotels are my preferred choice hotel, but this one does not meet the expectations whatsoever. It was filthy and needs a deep clean. The base of the toilet had urine stains, There were yellow stains all over the walls of the bathroom. Mold in the shower. The Nespresso machine with filthy. ...
Reviewed on Feb 21, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$92
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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- University of Pittsburgh
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- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
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- Walnut Street
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.